Yukka: What? Not at all. What I mean is, by that logic, what would you say about people attracted to the same sex? Because "love" isn't something that's only between guys and girls. Being in love with her doesn't mean you see her as a guy. Or is it that you fell in love with her because "Akira-chan is a guy"?
Dating can be hard for transgender characters.
Coming out to a partner (or potential partner) seems to be a make-it-or-break-it deal in many relationships. Whether the partner accepts their significant other or not varies. A variant on this occurs when someone transitions after they have already settled down. This almost always creates conflict with their partner and often their children if they have any. The issue of whether they should separate or not usually comes up.
Another trouble trans characters face is how society (or at least other people closest to them) looks on them. Society may not accept same-sex relationships and view the relationship between a cis woman and a trans man, or a cis man and a trans woman, as gay. As a result, they deal with homophobia as well as transphobia, regardless of their sexuality.
- Wandering Son:
- Nitori and Anna begin dating in middle school. Anna knew about Nitori wearing girl's clothes and was fine with it, but the full situation didn't dawn on her until Nitori tried to go to school dressed in the female uniform. The confusion led Anna to break up with Nitori, though they end up together again later. Everything ends up resolved when, before Nitori goes off to college, Anna tells Nitori that she likes her as a girl and she's fine being labeled lesbian if they're together.
- Makoto is a closeted trans girl who has a habit of falling in love with guys. However, she can't be open about her feelings because everyone sees her as a boy and she'd likely get rejected as a result. Her main crush throughout middle and high school is a bully named Oka. Oka doesn't notice Mako's feelings and gets weirded out when Mako tries to give him "friendship chocolates" on Valentine's Day. Later on, Oka sees Makoto at a restaurant in girl mode, however he didn't realize it was her. He inadvertently hurt her feelings later when he laughed at the idea of Makoto as a girl.
- Marika from Bokura no Hentai is stuck in a Betty and Veronica situation between the troubled Osamu and friendly Satoshi. Osamu was Marika's first crush and is mutually attracted to her, but he is gay and sees her as an effeminate boy. Satoshi becomes Marika's friend later in the manga and he is a bisexual boy who likes Marika either way. Marika doesn't end up with either but there's a heavy Maybe Ever After involving Satoshi.
- Subverted in one story in Mermaid Line. A couple breaks up when one decides to transition, however they end up back together again a few weeks later in an If It's You, It's Okay situation. The trans woman thinks her girlfriend is cheating on her with a man, but it turns out she had actually gotten a new job trying to buy a gift for her girlfriend.
- This gets in the way of Aoi's love life in You're Under Arrest!. She's a very attractive, very nice Dude Magnet but her being transgender always leads to men turning her down after she tells them.
- Played for Laughs in Stop Hibari Kun. Hibari is an Abhorrent Admirer because she's trans, but Kousaku still can't help but find her attractive nevertheless.
- Tetsuo from Yuureitou mentions that he can't date women because they always freak out when he comes out. He ends up dating his (male) best friend, Taichi, who was the first person to accept him as male even after coming out to him.
- The shoujo manga Go! Go! Ichigo! stars an elementary schooler with a crush on her Childhood Friend who she was recently reunited with. She's horrified by the fact Ichigo is now living as a girl, and throughout the manga she tries to out her to the class, but eventually she comes to terms with it all and begins dating Ichigo.
- The third story in the anthology Mascara Blues revolves around a young woman who has a crush on a hairdresser. She has a lot of angst about coming out to him as trans.
- Trans woman Kashiwa from Kyou Kara Yonshimai runs into this with her girlfriend. They're fine dating, but her girlfriend doesn't want Kashiwa to get surgery. She claims it's because it'll make marriage a more difficult process, but Kashiwa worries that it's because she sees her as a Wholesome Crossdresser instead of a woman.
- Protagonist Sara of Ai no Shintairiku falls in Love at First Sight with a boy at her new school but is Forced Out of the Closet by her homeroom teacher later that day. With everyone in school knowing she's transgender, it causes some turmoil. Her crush Kaito likes her back but goes through some confusion dealing with his attraction to her.
- Tooru Mutsuki from Tokyo Ghoul has an internalized version of this trope. He's attracted to a male character but is uncomfortable with it, thinking that it makes him female. This internalized angst also has to do with his Ambiguous Gender Identity; he's introduced as a transgender male but his identity gets muddled up as the manga goes on.
- A rare non-binary example appears in Love Me for What I Am. Mogumo is AMAB and feminine presenting, but they're neither a boy or a girl. Their male friend Tetsu has a crush on them. Kotone, who is a closeted lesbian and likes Mogumo herself, questions Tetsuo on this later. The two are male on paper, so they can't get married in Japan. Others see them as a gay couple, even if their relationship isn't same-gender.
- Hime from Kanojo ni Naritai Kimi to Boku is confused for her feelings towards her recently-out friend Akira. She worries that she subconsciously sees Akira as a boy, but a friend helps her realize that she does she Akira as a girl (though she wouldn't mind if Akira was cis either).
- One episode of Dirty Pair deals with the kidnapping of a corporate CEO's kid by the bodyguard the CEO fired - because they were starting to develop a relationship, and as a matter of fact the "kidnapping" turns out to be the two of them deciding to run away Romeo and Juliet-style. At the climax, the CEO reveals that the bodyguard is a male-to-female transexual in an attempt at making the kid give up, but the kid makes clear he doesn't gives a damn about that.
- Subverted in How Do I Admit I'm Falling Apart. Sonic worries about coming out to Amy because she's lesbian and likes him as a girl. However, it turns out his worries were for nothing when Amy reveals that she's actually bisexual, not gay.
- Subverted in RWBY: Scars. Jaune worries that his girlfriend Pyrrha won't like him after he comes out as a trans boy. He presumably came out off-screen and she didn't care.
- Sei in Metamorphosis is a lesbian. When the cute girl she kisses is outed as trans, Sei deals with confusion over her attraction.
- In the Pokémon fic Dark Secrets, Butch has second thoughts after having drunken sex with Cassidy. The next day, he freaks out and calls her a "freak" for being transgender. Cassidy ends up Driven to Suicide, though Jessie saves her.
- In Jigsaw, closeted trans boy Takatsuki bemoans that his crush Chiba wants a girlish boyfriend but sees him as a boyish girl.
- Different for Girls revolves around a post-op trans woman meeting a high school friend again. He's at first freaked out but eventually comes to accept her and falls for her.
- Used famously in The Crying Game, where main character Fergus freaks out and nearly abandons Dil after realizing that she's a trans woman.
- Boy Meets Girl examines a young trans woman in a small town dealing with various relationship troubles; a new female friend is attracted to her and worries over it making her a lesbian when they sleep together. Refreshingly, the characters discuss their feelings sensibly, without trying to hurt each other.
- J from I Am J ends up dating a girl called "Blue", however he doesn't tell her that he's transgender. He has a lot of internal conflict trying to hide it from her. Eventually she finds out by seeing him go to Harvey Milk High School. She initially assumes he's gay (which would explain his awkwardness towards her). After he comes out to her, they end up breaking up.
- Almost Perfect is about the protagonist's struggle to come to grips with his crush on the new transfer student, who he later learns is transgender
- In the book If I Was Your Girl, trans girl Amanda is outed to her boyfriend during a dance. He then asks if that makes him gay.
- The Coldest Girl in Coldtown features an interesting variation, Valentina is a trans woman who has a crush on her friend Jameson. One of the main reasons she won't pursue a relationship with him is that she's afraid if he found out about her being trans, he'd reject her. Turns out though that he also had a thing for her as well and that he genuinely doesn't care about that at all.
- The book Freakboy revolves around a teenager, Brandon, realizing and coming to terms with the fact that he is genderfluid. One of the main plotlines is the difficulty this causes in his relationship with his girlfriend Vanessa: in the end, it's ambiguous whether they'll still be lovers or Amicable Exes.
- One CSI episode involves a victim who never came out to her long-time boyfriend and was planning on getting SRS behind his back.
- In Freaks and Geeks, Seth Rogan's character learns his girlfriend was born intersex and spends time concerned about his sexuality (eventually deciding he's straight because he like rock music and girlie mags).
- In an infamous episode of The IT Crowd, Douglas dates April, a transgender reporter, who is pleased to find that he is so open-minded about accepting her gender reassignment. Unfortunately, it turns out that this was only due to One Dialogue, Two Conversations: When she told Douglas "I used to be a man," he was only half listening and thought she said "I'm from Iran." She proceeds to start a No-Holds-Barred Beatdown on him, crashing right through a shareholder meeting.
- Against Me!'s album Transgender Dysphoria Blues, an album full of Trans Tribulations born of frontwoman Laura Jane Grace's experience with the topic, has two songs that fit this trope:
- "Unconditional Love" is about a trans woman's relationship with her lover while struggling with dysphoria and frustration at media hounding of trans suicide.
- "FUCKMYLIFE 666" is, again, about a trans woman's relationship with her lover, this time concerning the relationship's stability in light of her transition.
- The Kinks classic "Lola" is about this from the perspective of a cis man who falls for a trans woman. The fourth verse sees him react rather poorly before asking forgiveness and declaring himself happy with the arrangement.
- Catherine: In the main story, one of Vincent's friends, Toby, has the hots for Erica, one of the servers at the Stray Sheep bar they attend. Eventually he manages to score a date and loses his virginity to her until his friends reveal that she was actually a former schoolmate friend named Eric who swapped genders. Naturally, Toby is mortified to learn this though for the most part, it doesn't seem to have strained his friendship with Erica other them some good-humored awkwardness.
- Khaos Komix: Charlie's arc mainly revolves around trying to tell her homophobic boyfriend that she's a trans woman.
- Zoe of Venus Envy deals with this early on. While on a date with a girl, the girl accidentally finds out that Zoe is transgender and freaks out. She gets upset and accuses Zoe of being a crossdresser trying to date a lesbian.
- Questionable Content: Discussed regarding Claire. She admits that transitioning didn't leave her the emotional space for romance and that she's never been kissed before dating Marten in their 20s, and her brother is concerned for her safety, but her relationship with Marten is happily uncomplicated.
- In Rain, Rain's brother Aiken stays at her and her aunt's place over Christmas because of "relationship troubles" with his fiancee. The issue is later revealed to be that Jessica, his fiancee, is a stealth trans woman, who was planning on having bottom surgery before they got married. When her insurance backed out, she was forced to come out to him, and he abandoned her.
- South Park: In "Go God Go", Garrison, at the time having changed into a woman (though save for some breasts and lipstick, looks exactly the same), enters into a relationship with evolutionary biologist Richard Dawkins, whom in the future Cartman travels to is revered as Dawkins' mate. When Eric tries to call back to the past to talk to Garrison, he lets slip of Garrison's sex-change operation. Dawkins is utterly repulsed when he finds out and breaks off the relationship.